


Pick-Up Line

by Center_of_the_Galaxy



Category: Supernatural
Genre: Bad Pick-Up Lines, Cross-Posted on Tumblr, Dean Winchester Is A Good Guy, Dean Winchester Plays Matchmaker For Sam and the Reader, Dean Winchester is Protective of Sam Winchester, Dean Winchester is Sam Winchester's Parent, F/M, Love Confessions, Pick-Up Lines, Sam Winchester is Bad at Feelings, Sam misunderstands, Sam thinks that the reader loves Dean, overheard love confession
Language: English
Status: Completed
Published: 2020-02-18
Updated: 2020-02-18
Packaged: 2021-02-27 20:54:13
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 806
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22782079
Author URL: https://archiveofourown.org/users/Center_of_the_Galaxy/pseuds/Center_of_the_Galaxy
Summary: You've finally worked up the nerve to ask Sam out, but Sam thinks you're more into Dean than him.
Relationships: Dean Winchester & You, Reader & Dean Winchester, Sam Winchester/Reader, Sam Winchester/You
Kudos: 55





	Pick-Up Line

“This is stupid.” 

“No, it’s not.” 

You rolled your eyes at Dean, facing him. You ran a hand through your hair, twisting a strand of it around your finger. You were nervous. You couldn’t help it. You sighed, “Dean.” 

Dean just chuckled, “Look. Who knows my brother better? You wanna try your pick-up line on Cas?” The eldest Winchester laughed, “That would go over well.” 

You sighed again, taking a seat at the table across from Dean. 

“Maybe I shouldn’t do this.” 

It had only been a few months since the Winchesters came barreling through your life. A random hunt had brought them to the door of your apartment and they’d save you from being attacked by a rampaging poltergeist. When you’d looked up into those deep eyes of Sam’s, you had fallen hard. Of course, after that night, you’d been sure you’d never see them ever again. 

But, life had a funny way of bringing you into Sam Winchester’s path. You and he kept meeting and after your apartment was overrun (again, to your dismay) with supernatural activity, the boys had taken you to their bunker. You didn’t understand a lot of their lives before now, but from what you did know, it had been rough. 

Maybe that was one of the reasons you’d felt drawn to Sam. You wanted to comfort him, to give him a safe space to let down his guard and cry on your shoulder. You wanted to give him everything, to be a support for him. 

But now, faced with the idea of actually telling him how you felt, how you were in love with him, you wanted to hide and never emerge. 

“Hey,” Dean placed a hand on your shoulder, his emerald eyes piercing deep, a reassuring smile on his lips, “My brother would be an idiot not to say yes.” 

You wanted to believe that, but it was such a delicate dance. If he said no, you knew everything would change. You would be heart-broken. 

“Okay,” You exhaled, shaky, facing him, “Let’s do this.” 

Dean beamed, “Great. Bring it on.” The eldest Winchester took a seat and faced you, smirking. 

“All right,” You braced yourself, replacing Dean’s face with Sam’s comforting visage, “I really like you. I would like to take the next step–” 

“No, no,” Dean waved you off, “Too formal. This ain’t a business deal.” He gestured toward you, “Try again.”

You swallowed nervously, “Please go out with me.” 

“Too desperate. Make him work for it.” 

“Dean–”

“Try again,” Dean pressed softly, “You can do this.” 

You sighed, trying to ground yourself. When it came down to it, you were just a girl, meeting a boy, trying to get him to go out with you. You could do this. You could be the girl who could sweep Sam off his feet. 

Just speak from the heart. Scary, but doable.

“When you saved me, I felt something. Maybe it was the concussion from being thrown by the ghost,” A chuckle escaped your lips, “But it just grew and grew. When you leave, I miss you. I want to hold your hand and listen to all about Greek monsters or whatever it is you’re researching. I just want to be with you. Do you want to be with me?”

Exhale. Relax. 

“Yes.” Dean answers, beaming. 

And Sam is suddenly standing there, eyes wide with shock and something that you can’t quite place. 

“Oh,” He mutters, looking down and you feel your heart sink, “Sorry. I didn’t mean to interrupt.” 

And then Sam is gone, long legs carrying him away from you. 

“Oh, shit.” Dean whispers. 

You can feel your heart breaking, feeling it crack in your chest, like broken glass.

“Hey,” Dean soothes, “I’ll talk to him, I can–”

But it’s not up to him. You’re not a damsel in distress waiting for a strong hunter to come in and save you. You rush past him, sprinting down corridors of the bunker, praying that you’re not getting lost. 

“Sam!” 

He turns around, his expression crestfallen. 

“Sorry,” He apologizes again, “I’m glad for you and Dean. You two will be–”

You launch yourself at him, lips pressing against his. Your eyes fall shut and you desperately hope that your actions will speak louder than misunderstood words. When you break off from him, you search his face, hoping that it’s not too late. 

“Sam, I–”

He just kisses you back, desperate and needy, hands in your hair, and you feel your heart soar. 

He pulls away, smiling, “You don’t like Dean?” 

“It was a misunderstanding. I was scared to tell you and Dean said I could practice on him and it was stupid, but I was afraid–”

“Hey,” Sam pulls you to him, wrapping his long arms around you, “I like you too.” 

And that’s all you need to hear. 


End file.
